US5039595A - Aqueous developer solution having hydroxy-alkyl piperidine for positive-working photoresists - Google Patents

Aqueous developer solution having hydroxy-alkyl piperidine for positive-working photoresists Download PDF

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Publication number
US5039595A
US5039595A US07/391,253 US39125389A US5039595A US 5039595 A US5039595 A US 5039595A US 39125389 A US39125389 A US 39125389A US 5039595 A US5039595 A US 5039595A
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United States
Prior art keywords
developer solution
positive
resist
aqueous developer
developing
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Ceased
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US07/391,253
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English (en)
Inventor
Reinhold Schwalm
Horst Binder
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BASF SE
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BASF SE
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Assigned to BASF AKTIENGESELLSCHAFT reassignment BASF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BINDER, HORST, SCHWALM, REINHOLD
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Publication of US5039595A publication Critical patent/US5039595A/en
Priority to US08/240,166 priority Critical patent/USRE35217E/en
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/005Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/42Developers or their precursors
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26Processing photosensitive materials; Apparatus therefor
    • G03F7/30Imagewise removal using liquid means
    • G03F7/32Liquid compositions therefor, e.g. developers
    • G03F7/322Aqueous alkaline compositions

Definitions

  • the present invention relates to an aqueous developer solution for positive-working photoresists, based on an aqueous solution of certain basic compounds which have excellent properties with regard to contrast, wall slope and resolution, and a method for development.
  • photoresists are used as an auxiliary layer in semiconductor technology.
  • Positive-working photoresists are preferably used for this purpose.
  • With the aid of the photoresists it is possible to produce relief images which leave the surface to be modified exposed in certain areas and thus make it accessible to further treatment, such as doping or metallization.
  • Positive resist images are produced by applying a layer of a photosensitive material to a silicon wafer and then exposing it through a structured mask and selectively dissolving away the exposed parts in the development process.
  • Conventional photosensitive compositions are those consisting of alkali-soluble resins, for example of the novolak type, and a photosensitive component, for example an o-quinonediazide.
  • alkali-soluble resins for example of the novolak type
  • a photosensitive component for example an o-quinonediazide.
  • the solubility of the composition in alkaline developers in the exposed parts is dramatically increased by the action of UV light.
  • the present invention relates to an aqueous developer solution for positive-working photoresists which contains a water-soluble basic compound, wherein the said compound is a compound of the general formula (I) ##STR2## where R 1 to R 5 are identical or different and are each H, OH, hydroxyalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms and x is from 1 to 5.
  • This developer solution may additionally contain a nonionic surfactant.
  • the novel developer solution contains in general from 5 to 50, preferably from 10 to 40, % by weight, based on the total amount of the developer solution, of a compound of the formula (I).
  • Particularly preferred hydroxyalkylpiperidines of the general formula (I) are N-hydroxymethyl-, N-hydroxyethyl-and N-hydroxypropylpiperidine.
  • the present invention furthermore relates to a method for developing a positive-working photoresist based on novolak/o-quinonediazide, the resist being applied to a substrate, exposed imagewise and brought into contact with developer solution to form the positive resist image, and the developer solution used being a novel aqueous developer solution, and a method for developing a positive-working photoresist based on poly-(p-hydroxystyrene)/sulfonium salt, a similar process being adopted with the use of the novel developer solution.
  • the developer solutions according to the invention have improved stability and development capacity. They therefore make it possible to achieve excellent properties with regard to contrast, wall slope and resolution.
  • the novel developer can be used in principle to develop all positive photoresist materials which are essentially based on mixtures of phenolic resins, as the base-soluble matrix, and a photosensitive component.
  • Such materials are, for example, the known positive resists based on novolaks and compounds of the naphthoquinonediazide type.
  • novolaks in positive resists are given by T. Pampalone in Solid State Technology, June 1984, pages 115-120.
  • developer for positive resists based on the systems described in DE-A-37 21 741 and consisting of phenolic polymers and onium salts having acid-labile groups.
  • Preferred onium salts are sulfonium salts of the general formula (II) ##STR3## where R 1 to R 3 are identical or different and may each contain aromatic and/or aliphatic radicals which may contain heteroatoms, with the proviso that one or more of the radicals R 1 to R 3 contains an acid-cleavable group, for example a tert-butyl carbonate of a phenol or a silyl ether of a phenol.
  • acid-labile groups are preferred, but a large number of other acid-labile groups, such as the known tetrahydropyranyl ethers, ortho esters, trityl and benzyl groups and tert-butyl esters of carboxylic acids, may also be used. It is also possible for two or more sulfonium units in the molecule to be linked via the radicals R 1 to R 3 .
  • Preferred counter-ions X.sup. ⁇ are complex metal halides, such as tetrafluoborate, hexafluoroantimonate, hexafluoroarsenate and hexafluorophosphate.
  • the phenolic polymers contain, as a rule, units of the general formula (III) ##STR4## where R is hydrogen, halogen or alkyl of 1 to 4 carbon atoms, R 4 , R 5 , R 6 and R 7 are each hydrogen, halogen or alkyl or alkoxy, each of 1 to 4 carbon atoms, R 8 is hydrogen or an acid-labile group, such as trimethylsilyl, tert-butoxycarbonyl, isopropoxycarbonyl or tetrahydropyranyl, and x is from 1 to 3, preferably 1.
  • Preferred polymers of the formula (III) are those where R is hydrogen or methyl and R 4 to R 7 are each hydrogen and the radicals R 8 are hydrogen and/or an acid-labile group having one of the abovementioned meanings, --O--R 8 being in the p-position and the proportion of groups where R 8 is hydrogen being not less than 70 mol %.
  • These polymers generally have mean molecular weights (M n ) of from 1,000 to 250,000, preferably from 10,000 to 80,000, and are generally present in the radiation-sensitive mixture in an amount of from 40 to 98, preferably from 60 to 95, % by weight.
  • Binders having a high aromatic content have the advantage that they are relatively stable in plasma etching processes and reactive ion etching processes.
  • the radiation-sensitive mixture may be necessary for the radiation-sensitive mixture to contain both a phenolic polymer based on polyvinylphenol and a novolak of the p-cresol/formaldehyde type, or predominantly o,o'-bonded phenol/formaldehyde, since one of these components alone frequently does not provide all the desired properties.
  • novel developer is also suitable for positive resists based on 3-component systems, consisting of an alkali-soluble binder, a compound which forms a strong acid when exposed to actinic radiation and a compound having one or more C--O--C bonds cleavable by an acid, as described in, for example, DE-A-3406927.
  • the novel process for producing resist images is carried out in a known manner but with the use of the novel developer.
  • the mixtures of phenolic resin and/or phenolic polymer and photosensitive component are generally dissolved in an organic solvent, the solids content being from 5 to 40% by weight.
  • Preferred solvents are aliphatic ketones, ethers and esters, and mixtures of these.
  • Alkylene glycol monoalkyl ethers for example ethylcellosolve, butyglycol, methylcellosolve and 1-methoxy-2-propanol
  • alkylene glycol alkyl ether esters for example methylcellosolve acetate, ethylcellosolve acetate, methylpropylene glycol acetate and ethylpropylene glycol acetate
  • ketones for example cyclohexanone, cyclopentanone and methyl ethyl ketone
  • acetates such as butyl acetate
  • aromatics such as toluene and xylene
  • additives such as adhesion promoters, wetting agents, dyes and plasticizers, may also be added.
  • sensitizers may, if necessary, also be added in order to sensitize the compounds in the relatively long-wavelength UV to the visible range.
  • Polycyclic aromatics such as pyrene and perylene, are preferred, but it is also possible to use other dyes which act as sensitizers.
  • the homogeneous solution of the photosensitive mixture can be applied in a conventional manner, for example by spin coating, to the substrate to be coated, in general to a silicon wafer oxidized on the surface, so that a photosensitive layer having a thickness of about 1-2 ⁇ m is obtained, and can be heated at from 60° to 120° C.
  • suitable light sources being, for example, high pressure mercury lamps or excimer lasers, a latent image is produced in the photosensitive layer.
  • a postexposure bake can, if required, also be carried out, at from 60° to 120° C.
  • this postexposure bake is carried out in some cases to reduce the effects due to standing waves; in the case of systems based on poly-(p-hydroxystyrene)/sulfonium salt, however, a postexposure bake at from 60° to 120° C. is essential.
  • surfactants it is not necessary to add surfactants to the novel developer solution.
  • such substances may be added in general in amounts of not more than 5% by weight, based on the total amount of the developer solution, for example nonylphenoxypoly-(ethyleneoxy)-ethanol, octylphenoxypoly-(ethyleneoxy)-ethanol or commercial fluorinated surfactants.
  • the relief produced is dried and then serves as the mask for the further treatment steps, such as etching of the substrate.
  • the novel developer has excellent properties with regard to the resolution to be achieved (less than 1 ⁇ m) and wall slope, permits high sensitivity of the resist to short-wavelength UV radiation, has good development capacity and stability and is therefore ideal for microlithography for the production of semiconductor components.
  • a commercial positive resist based on novolak/naphthoquinonediazide was applied to surface-oxidized silicon wafers by spin coating, in such a way that, after the wet polymer layer had been dried at 90° C. on a hot plate, 1 ⁇ m thick resist layers resulted.
  • the wafers were then exposed in a contact exposure unit through a chromium-coated quartz plate having variable transmission areas and were developed in the downstream development process at 21° C. in 40% strength N-(2-hydroxyethyl)-piperidine solution, the exposed photoresist parts being dissolved. No undesirable residues were detectable on the photoresist images or the exposed developed areas after thorough washing with deionized water.
  • Exposure of the coated and predried silicon wafers through the transmission mask was carried out using short-wavelength UV light of wavelength 248 nm, by the contact process under reduced pressure. Following thermal aftertreatment for 1 minute at 100° C., the silicon wafers could be developed in 20% strength N-(2-hydroxyethyl)-piperidine solution of pH 12.4.
  • the layer thicknesses were measured using an ⁇ -step profilometer from Tencor.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
US07/391,253 1988-08-13 1989-08-09 Aqueous developer solution having hydroxy-alkyl piperidine for positive-working photoresists Ceased US5039595A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US08/240,166 USRE35217E (en) 1988-08-13 1994-05-09 Aqueous developer solution having hydroxy-alkyl piperidine for positive-working photoresists

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3827567 1988-08-13
DE3827567A DE3827567A1 (de) 1988-08-13 1988-08-13 Waessrige entwicklerloesung fuer positiv arbeitende photoresists

Related Child Applications (1)

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US08/240,166 Reissue USRE35217E (en) 1988-08-13 1994-05-09 Aqueous developer solution having hydroxy-alkyl piperidine for positive-working photoresists

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US5039595A true US5039595A (en) 1991-08-13

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US07/391,253 Ceased US5039595A (en) 1988-08-13 1989-08-09 Aqueous developer solution having hydroxy-alkyl piperidine for positive-working photoresists
US08/240,166 Expired - Lifetime USRE35217E (en) 1988-08-13 1994-05-09 Aqueous developer solution having hydroxy-alkyl piperidine for positive-working photoresists

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US (2) US5039595A (ja)
EP (1) EP0355015B1 (ja)
JP (1) JPH02103549A (ja)
KR (1) KR900003676A (ja)
CA (1) CA1335338C (ja)
DE (2) DE3827567A1 (ja)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5821036A (en) * 1995-01-20 1998-10-13 Clariant Finance (Bvi) Limited Method of developing positive photoresist and compositions therefor
US6017766A (en) * 1998-01-28 2000-01-25 Clariant Finance (Bvi) Limited Process for measuring concentration of nonionic surfactants in an aqueous alkaline solution
US6127101A (en) * 1999-10-12 2000-10-03 Air Products And Chemicals, Inc. Alkylated aminoalkylpiperazine surfactants and their use in photoresist developers
US6268115B1 (en) 2000-01-06 2001-07-31 Air Products And Chemicals, Inc. Use of alkylated polyamines in photoresist developers
US6403499B2 (en) * 1998-10-22 2002-06-11 Micron Technology, Inc. Planarization of non-planar surfaces in device fabrication
US6693034B2 (en) 1997-05-23 2004-02-17 Micron Technology, Inc. Deadhesion method and mechanism for wafer processing
US20040170917A1 (en) * 2001-06-12 2004-09-02 Shuichi Takahashi Method of forming thick resist pattern
US20040209475A1 (en) * 1997-05-23 2004-10-21 Doan Trung T. Planarization process for semiconductor substrates
US20080138747A1 (en) * 2003-10-06 2008-06-12 Hynix Semiconductor Inc. Method for Forming a Photoresist Pattern

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100670090B1 (ko) * 2000-11-29 2007-01-17 신에쓰 가가꾸 고교 가부시끼가이샤 아민 화합물, 레지스트 재료 및 패턴 형성 방법
CN103197516A (zh) * 2013-04-18 2013-07-10 合肥格林达电子材料有限公司 光蚀刻用复合显影液

Citations (12)

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Publication number Priority date Publication date Assignee Title
US4192929A (en) * 1978-08-31 1980-03-11 Ford Motor Company Corrosion resistant primers
EP0080042A1 (en) * 1981-09-28 1983-06-01 Fuji Photo Film Co., Ltd. Method for the development of photoresist layers, and developer
EP0124297A2 (en) * 1983-04-01 1984-11-07 Sumitomo Chemical Company, Limited Alkaline solution for developing positive photoresists
US4576903A (en) * 1983-12-24 1986-03-18 Merck Patent Gesellschaft Mit Beschrankter Haftung Developer for positive photoresists
EP0231028A2 (en) * 1986-01-29 1987-08-05 MicroSi, Inc. (a Delaware corporation) High contrast low metal ion photoresist developing method and composition
WO1987007039A2 (en) * 1986-05-14 1987-11-19 Eastman Kodak Company High contrast development of photographic elements
GB2193335A (en) * 1986-07-18 1988-02-03 Tokyo Ohka Kogyo Co Ltd A developer solution for positive-working photoresist compositions
US4833067A (en) * 1985-08-06 1989-05-23 Tokyo Ohka Kogyo Co., Ltd. Developing solution for positive-working photoresist comprising tmah and non-ionic surfactant
US4863828A (en) * 1987-01-20 1989-09-05 Fuji Photo Film Co., Ltd. Positive-working o-quinone diazide photoresist composition
EP0336400A2 (en) * 1988-04-07 1989-10-11 Fuji Photo Film Co., Ltd. Developer for dry ps plates
US4877719A (en) * 1985-10-18 1989-10-31 Fuji Photo Film Co., Ltd. Process for preparing image-bearing plates
US4929605A (en) * 1987-10-07 1990-05-29 Merrell Dow Pharmaceuticals Inc. Pharmaceutical composition for piperidinoalkanol derivatives

Patent Citations (14)

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Publication number Priority date Publication date Assignee Title
US4192929A (en) * 1978-08-31 1980-03-11 Ford Motor Company Corrosion resistant primers
EP0080042A1 (en) * 1981-09-28 1983-06-01 Fuji Photo Film Co., Ltd. Method for the development of photoresist layers, and developer
EP0124297A2 (en) * 1983-04-01 1984-11-07 Sumitomo Chemical Company, Limited Alkaline solution for developing positive photoresists
US4576903A (en) * 1983-12-24 1986-03-18 Merck Patent Gesellschaft Mit Beschrankter Haftung Developer for positive photoresists
US4833067A (en) * 1985-08-06 1989-05-23 Tokyo Ohka Kogyo Co., Ltd. Developing solution for positive-working photoresist comprising tmah and non-ionic surfactant
US4877719A (en) * 1985-10-18 1989-10-31 Fuji Photo Film Co., Ltd. Process for preparing image-bearing plates
EP0231028A2 (en) * 1986-01-29 1987-08-05 MicroSi, Inc. (a Delaware corporation) High contrast low metal ion photoresist developing method and composition
WO1987007039A2 (en) * 1986-05-14 1987-11-19 Eastman Kodak Company High contrast development of photographic elements
GB2193335A (en) * 1986-07-18 1988-02-03 Tokyo Ohka Kogyo Co Ltd A developer solution for positive-working photoresist compositions
US4820621A (en) * 1986-07-18 1989-04-11 Tokyo Ohka Kogyo Co., Ltd. Developer solution for positive-working photoresist compositions comprising a base and a non-ionic surfactant
US4820621B1 (ja) * 1986-07-18 1991-03-12 Tokyo Ohka Kogyo Co Ltd
US4863828A (en) * 1987-01-20 1989-09-05 Fuji Photo Film Co., Ltd. Positive-working o-quinone diazide photoresist composition
US4929605A (en) * 1987-10-07 1990-05-29 Merrell Dow Pharmaceuticals Inc. Pharmaceutical composition for piperidinoalkanol derivatives
EP0336400A2 (en) * 1988-04-07 1989-10-11 Fuji Photo Film Co., Ltd. Developer for dry ps plates

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* Cited by examiner, † Cited by third party
Title
Aldrich Chemical Catalog p. 1065. *
Evaluation of Pure Novolak Cresol Formaldehyde Resins for Deep U.V. Lithography, Gipstein et al., J. Chem. Soc. Jan. 1982, 201 205. *
Evaluation of Pure Novolak Cresol-Formaldehyde Resins for Deep U.V. Lithography, Gipstein et al., J. Chem. Soc. Jan. 1982, 201-205.
Novolac Resins Used in Positive Resist Systems, T. R. Pampalone, Solid State Technology, Jun. 1984, pp. 115 120. *
Novolac Resins Used in Positive Resist Systems, T. R. Pampalone, Solid State Technology, Jun. 1984, pp. 115-120.

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5821036A (en) * 1995-01-20 1998-10-13 Clariant Finance (Bvi) Limited Method of developing positive photoresist and compositions therefor
US6693034B2 (en) 1997-05-23 2004-02-17 Micron Technology, Inc. Deadhesion method and mechanism for wafer processing
US20040209475A1 (en) * 1997-05-23 2004-10-21 Doan Trung T. Planarization process for semiconductor substrates
US20060249723A1 (en) * 1997-05-23 2006-11-09 Doan Trung T Planarization process for semiconductor substrates
US6017766A (en) * 1998-01-28 2000-01-25 Clariant Finance (Bvi) Limited Process for measuring concentration of nonionic surfactants in an aqueous alkaline solution
US6403499B2 (en) * 1998-10-22 2002-06-11 Micron Technology, Inc. Planarization of non-planar surfaces in device fabrication
US6677252B2 (en) 1998-10-22 2004-01-13 Micron Technology, Inc. Methods for planarization of non-planar surfaces in device fabrication
US6127101A (en) * 1999-10-12 2000-10-03 Air Products And Chemicals, Inc. Alkylated aminoalkylpiperazine surfactants and their use in photoresist developers
US6268115B1 (en) 2000-01-06 2001-07-31 Air Products And Chemicals, Inc. Use of alkylated polyamines in photoresist developers
US20040170917A1 (en) * 2001-06-12 2004-09-02 Shuichi Takahashi Method of forming thick resist pattern
US20080138747A1 (en) * 2003-10-06 2008-06-12 Hynix Semiconductor Inc. Method for Forming a Photoresist Pattern
US7781145B2 (en) * 2003-10-06 2010-08-24 Hynix Semiconductor Inc. Method for forming a photoresist pattern

Also Published As

Publication number Publication date
EP0355015A2 (de) 1990-02-21
EP0355015B1 (de) 1994-01-19
USRE35217E (en) 1996-04-23
EP0355015A3 (en) 1990-05-30
KR900003676A (ko) 1990-03-26
DE3827567A1 (de) 1990-02-22
DE58906742D1 (de) 1994-03-03
JPH02103549A (ja) 1990-04-16
CA1335338C (en) 1995-04-25

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